They make breaking changes to settings (and possibly data stores, but I forget) between versions, so to go from, for example, x.y.1 to x.z.5 might involve doing migrations between x.y.2 through x.z.5 just to use the latest version.

This is not the case for all versions, but I've found it to be common enough that I have to read all of the release notes between point versions when upgrading.

It can definitely be improved.